Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1623)
Drug Name
Toremifene citrate
Synonyms
Toremifene (Citrate); Toremifene Citrate (Fareston, Acapodene); Toremifene citrate [USAN]; Toremifene Base; Toremifene [INN:BAN]; Toremifeno; Toremifeno [Spanish]; Toremifenum; Toremifenum [Latin]; UNII-7NFE54O27T; Z-Toremifene; toremifene; {2-[4-(4-Chloro-1,2-diphenyl-but-1-enyl)-phenoxy]-ethyl}-dimethyl-amine; 2-(para-((Z)-4-Chloro-1,2-diphenyl-1-butenyl)phenoxy)-N,N-dimethylethylamine (IUPAC); 2-[4-[(Z)-4-chloro-1,2-diphenylbut-1-enyl]phenoxy]-N,N-dimethylethanamine; 7NFE54O27T; 89778-26-7; Acapodene; C26H28ClNO; CHEBI:9635; FC-1157a; Farestone; GTx 006; UNII-2498Y783QT; (Z)-4-Chloro-1,2-diphenyl-1-(4-(2-(N,N-dimethylamino)ethoxy)phenyl)-1-butene citrate (1:1); 2-(p-((Z)-4-Chloro-1,2-diphenyl-1-butenyl)phenoxy)-N,N-dimethylethylamine citrate (1:1); 2498Y783QT; 89778-27-8; CCRIS 6719; CPD000469213; DSSTox_CID_1367; DSSTox_GSID_21367; DSSTox_RID_76113; FC 1157a; Fareston; NK 622; NSC 613680; NSC613680; TOREMIFENE CITRATE
Indication Breast cancer [ICD11: 2C60] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 598.1 Topological Polar Surface Area 145
Heavy Atom Count 42 Rotatable Bond Count 14
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
3005572
ChEBI ID
CHEBI:9636
CAS Number
89778-27-8
TTD Drug ID
D04VFJ
Formula
C32H36ClNO8
Canonical SMILES
CN(C)CCOC1=CC=C(C=C1)C(=C(CCCl)C2=CC=CC=C2)C3=CC=CC=C3.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
InChI
1S/C26H28ClNO.C6H8O7/c1-28(2)19-20-29-24-15-13-23(14-16-24)26(22-11-7-4-8-12-22)25(17-18-27)21-9-5-3-6-10-21;7-3(8)1-6(13,5(11)12)2-4(9)10/h3-16H,17-20H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/b26-25-;
InChIKey
IWEQQRMGNVVKQW-OQKDUQJOSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Bisphenol TOR DM002339
11405425
Unclear 1 [3]
N-demethyl-toremifene DM002335
3035212
Unclear 1 [4]
Z-4-hydroxy TOR DM002341
71749350
Unclear 1 [3]
4-hydroxy-N-Desmethyl TOR DM002338
3036500
Unclear 2 [3]
Bisphenol TOR DM002339
11405425
Unclear 2 [3]
Carboxylated metabolites DM002340 N. A. Unclear 2 [3]
Deaminohydroxy TOR DM002336
3036505
Unclear 2 [3]
E-4-hydroxy Toremifene DM002342
10669899
Unclear 2 [3]
4-hydroxy-N-Desmethyl TOR DM002338
3036500
Unclear 3 [3]
Toremifene citrate Carboxylated metabolites DM002337 N. A. Unclear 3 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002420 Toremifene citrate N-demethyl-toremifene Unclear CYP3A4 [4]
MR002421 Toremifene citrate Bisphenol TOR Unclear Unclear [3]
MR002422 Toremifene citrate Z-4-hydroxy TOR Unclear Unclear [3]
MR002416 Bisphenol TOR Carboxylated metabolites Unclear Unclear [3]
MR002413 N-demethyl-toremifene Deaminohydroxy TOR Unclear Unclear [3]
MR002417 Z-4-hydroxy TOR 4-hydroxy-N-Desmethyl TOR Unclear Unclear [3]
MR002418 Z-4-hydroxy TOR Bisphenol TOR Unclear Unclear [3]
MR002419 Z-4-hydroxy TOR E-4-hydroxy Toremifene Unclear Unclear [3]
MR002414 Deaminohydroxy TOR Toremifene citrate Carboxylated metabolites Unclear Unclear [3]
MR002415 Deaminohydroxy TOR 4-hydroxy-N-Desmethyl TOR Unclear Unclear [3]
⏷ Show the Full List of 10 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 Toremifene Citrate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Involvement of cytochrome P450 3A enzyme family in the major metabolic pathways of toremifene in human liver microsomes. Biochem Pharmacol. 1994 May 18;47(10):1883-95.
3 Clinical pharmacokinetics of toremifene Clin Pharmacokinet. 2000 Nov;39(5):327-34. doi: 10.2165/00003088-200039050-00002.
4 Toremifene in postmenopausal breast cancer. Efficacy, safety and cost Drugs Aging. 1997 Oct;11(4):261-70. doi: 10.2165/00002512-199711040-00002.

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